1-hydroxy-1,3-diphenylpropan-2-one | 41049-36-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-hydroxy-1,3-diphenylpropan-2-one
• 英文别名: (1R)-1-hydroxy-1,3-diphenylpropan-2-one
• CAS: 41049-36-9
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: SSCJKWMZFNHATQ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-hydroxy-1,3-diphenylpropan-2-one 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 以48.8 mg的产率得到2-oxo-1,3-diphenylpropyl acetate
  参考文献：
  名称：

  Al Lewis acid-catalyzed regiodivergent 1,2-rearrangement of α-siloxy aldehydes: scope and mechanism

  摘要：

  Regiodivergent 1,2-rearrangement of alpha-siloxy aldehydes bearing alpha-aryl and alpha-alkyl substituents into alpha-siloxy ketones has been realized by using different Al Lewis acid catalyst/solvent systems. The scope of this unprecedented protocol has been investigated with various substrates, clearly demonstrating its utility for the selective synthesis of two structural isomers from one substrate. Controlled experiments proved that the regiodivergency resulted from the switch of the migrating group. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.126
• 作为产物：
  描述：

  (R)-1,3-diphenyl-1-(triethylsiloxy)propan-2-one 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-hydroxy-1,3-diphenylpropan-2-one
  参考文献：
  名称：

  Al Lewis acid-catalyzed regiodivergent 1,2-rearrangement of α-siloxy aldehydes: scope and mechanism

  摘要：

  Regiodivergent 1,2-rearrangement of alpha-siloxy aldehydes bearing alpha-aryl and alpha-alkyl substituents into alpha-siloxy ketones has been realized by using different Al Lewis acid catalyst/solvent systems. The scope of this unprecedented protocol has been investigated with various substrates, clearly demonstrating its utility for the selective synthesis of two structural isomers from one substrate. Controlled experiments proved that the regiodivergency resulted from the switch of the migrating group. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.126

文献信息

• Enantioselective synthesis of protected α-hydroxy aldehydes and ketones via hydroxylation of metalated chiral hydrazones
  作者：Dieter Enders、Vidya Bhushan

  DOI：10.1016/s0040-4039(00)87901-0

  日期：1988.1

  α-Benzyloxy aldehydes and α-acetoxy ketones 4 of high enantiomeric purity are prepared in good overall yields via oxaziridine mediated hydroxylation of chiral hydrazone azaenolates. As auxiliaries novel proline derived hydrazine reagents 5 are used.

  高的对映体纯度的α-苄氧基醛和α-乙酰氧基酮4通过恶唑烷介导的手性氮杂酸酯的羟基化反应以良好的总收率制备。作为助剂，使用了新的脯氨酸衍生的肼试剂5。
• Enantioselective Aerobic Oxidation of α-Hydroxy-Ketones Catalyzed by Oxidovanadium(V) Methoxides Bearing Chiral, <i>N</i>-Salicylidene-<i>tert</i>-butylglycinates
  作者：Chien-Tien Chen、Jun-Qi Kao、Santosh B. Salunke、Ya-Hui Lin

  DOI：10.1021/ol1024053

  日期：2011.1.7

  Chiral oxidovanadium(V) methoxides prepared from 3,5-disubstituted-N-salicylidene-l-tert-butylglycines and vanadyl sulfate in air-saturated MeOH serve as highly enantioselective catalysts for asymmetric aerobic oxidations and kinetic resolution of alkyl, aryl, and heteroaryl α-hydroxy-ketones with differed α-substituents at ambient temperature in toluene or TBME (tert-butyl methyl ether). The best

  手性oxidovanadium（V）甲醇盐由3,5-二取代制备Ñ -salicylidene-升-叔-butylglycines和硫酸氧钒在空气饱和的MeOH中服务于非对称需氧氧化和烷基的动力学拆分为对映体选择性高的催化剂，芳基，和杂芳基在室温下在甲苯或TBME（叔丁基甲基醚）中具有不同α-取代基的α-羟基酮。最佳方案包括使用带有衍生自3,5-二苯基-或3-邻-联苯-5-硝基-水杨醛的tridendate模板的配合物。基于选择性因子（k rel），好氧氧化过程的动力学分辨率选择性在12至> 1000的范围内。）。
• Complete Switch of Migratory Aptitude in Aluminum‐Catalyzed 1,2‐Rearrangement of Differently α,α‐Disubstituted α‐Siloxy Aldehydes
  作者：Kohsuke Ohmatsu、Takayuki Tanaka、Takashi Ooi、Keiji Maruoka

  DOI：10.1002/anie.200800801

  日期：2008.6.27
• Al Lewis acid-catalyzed regiodivergent 1,2-rearrangement of α-siloxy aldehydes: scope and mechanism
  作者：Kohsuke Ohmatsu、Takayuki Tanaka、Takashi Ooi、Keiji Maruoka

  DOI：10.1016/j.tet.2009.06.126

  日期：2009.9

  Regiodivergent 1,2-rearrangement of alpha-siloxy aldehydes bearing alpha-aryl and alpha-alkyl substituents into alpha-siloxy ketones has been realized by using different Al Lewis acid catalyst/solvent systems. The scope of this unprecedented protocol has been investigated with various substrates, clearly demonstrating its utility for the selective synthesis of two structural isomers from one substrate. Controlled experiments proved that the regiodivergency resulted from the switch of the migrating group. (C) 2009 Elsevier Ltd. All rights reserved.